| Date | From | To | Departure | Arrival | Status | |
|---|---|---|---|---|---|---|
| Aug 02 | BOS | MDW | 00:17 | 01:24 |
Delayed
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| Jul 26 | BOS | MDW | 23:30 | 00:29 |
Landed Late
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| Jul 19 | BOS | MDW | 22:57 | 00:02 |
Landed
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| Jul 12 | BOS | MDW | 23:15 | 00:10 |
Landed Late
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| Jul 05 | BOS | MDW | 23:34 | 00:39 |
Landed Late
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| Jun 28 | BOS | MDW | 23:22 | 00:29 |
Landed Late
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| Jun 21 | BOS | MDW | 00:18 | 01:30 |
Delayed
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| Jun 14 | BOS | MDW | 22:21 | 23:42 |
Landed
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| Jun 07 | BOS | MDW | 23:45 | 00:36 |
Delayed
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Southwest Airlines Flight WN585 connects Boston, United States to Chicago, United States, taking off from Boston Logan International Airport BOS and landing at Chicago Midway International Airport MDW.
How long is the WN585 flight from Boston to Chicago?
The average flight time from Boston to Chicago is 2 hours and 4 minutes. The flight distance is 1381 km / 858 miles and the average flight speed is 668 km/h / 415 mph.
What is the On-Time Performance (OTP) of Southwest Airlines Flight WN585 Boston to Chicago?
The Airportia On-Time Performance Rating for Southwest Airlines Flight WN585 is 4.2/5 stars. This metric is calculated using data from the past 10 flights.
When was the latest WN585 flight?
The latest flight took off on Monday, August 3rd, 2026 with the flight status being En-Route on 01:24.
How else can the flight WN585 be referenced as?
This Southwest Airlines flight can also be referenced as SWA585, WN0585, WN 585, SWA 585.
How often is flight WN585 delayed?
On average, 89% of all WN585 flights are delayed. The average delay is 51 minutes.
Can I get compensation for my delayed or cancelled WN585 flight or baggage issues?
If your WN585 flight was cancelled, delayed, or if you experienced baggage issues such as delayed, damaged, or lost bags, you may be entitled to compensation. Compensation amounts and eligibility depend on various regulations, including EC 261/2004, UK261, CA Montreal Convention, US GoodWill, BR-ANAC, SA-GACA and TK-SHY.
See our WN585 Flight Tracker above for more details.
Other flights departing from Boston BOS: WN736, DL5840, UA3757, WN3239
Other flights arriving at Chicago MDW: WN4762, WN1615, WN2044, WN578
All flights connecting Boston BOS to Chicago MDW.